Prohibited Love
by imperfectfairytale
Summary: AU 1920's C/B - Chuck Bass is New York's finest speakeasy owner with his uncle Jack owning the rival 21 club. Blair Waldorf is 21's headline act bringing in success and Chuck will go to any lengths to have her leave 21 and perform at Victrola...
1. Jack Ass

I've always wanted to write a 1920's CB fic because they would just be perfect in that era so I've tried to make it as 20's as I possibly can! The first chapter is quite vague and sets the scene for the rest of the story really.

So enjoy and please leave a review!

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**Prohibited Love**

_AU Chuck and Blair – Set in the 1920's prohibition era, Chuck Bass is New York's finest speakeasy owner. Blair Waldorf is the rival speakeasy's headline singer and Chuck will go to any lengths to have her perform at his club. Add in the fact that Chuck's uncle Jack is the owner of the rival speakeasy and the attraction between Chuck and Blair, and you will have yourself a much prohibited love indeed._

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**Chapter One** - _Jack-ass_

Chuck Bass put out his cigar into his marbled ashtray and picked up his gold engraved pen. He let out a deep sigh and inscribed his elaborate signature onto the bottom of one of the many contracts he needed to sign. Chuck was the owner of Victrola, Manhattan's most elite speakeasy and business had never been more booming. People relied on Chuck for a good time. They came for the sensual dancers, the bright lights and most importantly – the fine wines and prohibited spirits.

It was always in Chuck's nature to rebel against the rules. Even government laws couldn't stop him doing what he loved doing the most. Chuck was a businessman and a very fine one at that. Business meant money, and money most importantly meant power. Perhaps that was a trait he had inherited from his late father, the vindictive Bart Bass, who to Chuck made his life a living hell. It was from Bart that Chuck had inherited Bass Industries and Victrola was Chuck's first pursuit to show _dear old Dad_ that he could make it on his own.

Victrola was a place where individuals could come to forget about themselves and create someone completely different - someone who they wanted to be. It suited Chuck perfectly. Night after night he would become lost with the beautiful women with beautiful bodies who would come to Victrola. Sure, the names he could recall would be limited to one hand but names to Chuck didn't matter. With the women, came the alcohol and Chuck had plenty.

"Chuck, your uncle's here to see you". His closest friend and best bartender, Nate said as he popped his head through the door. Nate could make any cocktail, spirit or shot in the book plus many of his own concoctions. He was a vital asset to Victrola and it just so helped that the two of them had been friends since childhood.

"Don't call him that, Nathaniel. We talked about this; he's no family of mine." Chuck replied, a hint of resentment in his tone. He put down his pen and straightened his dark purple bowtie.

"Sorry, _Jack's_ here to see you," Nate apologised, "Should I send him in?"

Chuck nodded and prepared himself for the '_Jack-ass'_ that was about to enter his office. Sure, by unnecessary biological genes Jack was his uncle but to Chuck he had no family. His mother had died giving birth to him, his father was dead to him all his life anyway until he had passed, and his uncle schemed and plotted to take Chuck's inheritance ever since the day his brother had died. _'Some family'_, Chuck thought to himself bitterly.

"Charles," Jack greeted him in a demeaning tenor. "How are things?" Jack took a seat in the leather-cushioned chair opposite Chuck's desk. Chuck stared at him fiercely.

"What do you want, Jack?" He replied bitterly, leaning back into his chair. He folded his right leg on top of his left. This meant business.

"What? A man can't come and visit his nephew on a fine day like this?" Jack said with a patronising tone filled with false innocence. Chuck knew better.

"Not when the uncle is a conniving bastard out to get his nephew's inheritance, he can't". Chuck stood up and went over to his liqueur cabinet. He poured himself a scotch on the rocks and returned back to his seat.

Jack smiled at him with a sense of awareness. He narrowed his eyes and leant forward slightly in his chair. Chuck took a gulp of his scotch and placed the glass onto the marble desk.

"How's business these days, Charles?"

"Couldn't be better," Chuck didn't take his eyes off Jack. He was up to something.

"Heard about your singer, what a shame." Jack remarked. His tone couldn't have been less considerate if he tried. Chuck shrugged his shoulders.

"The least of our worries." Chuck remarked guardedly. "From what I've been hearing, Victrola's been spanking 21 in alcohol sales for the last couple of months now, singer or no singer." Chuck's eyes blackened with triumph. It was true, Victrola had been more successful than Jack's 21 Club since spring.

Jack smiled and looked down. "Not for long."

"And how do you expect to do that, Jack?" Chuck sneered, "People choose Victrola over 21 because it has panache, flair and style. They come to escape. Your little club on the other hand is filled with the desolate bastards who go for a tipple to drown their tears and the aspiring prostitutes who are welcomed with a quick fuck in the latrines. Face it, Victrola is class and 21 is trash. The truth hurts _Uncle_." The last utterance was filled with spite and malice. Chuck took another sip of his scotch whilst Jack simply stared at him, the smirk still etched onto his expression.

"Interesting observation, Charles." Chuck lifted his glass up and tilted his head towards Jack. "Thursday night. Come to 21 and you'll see for yourself just why you should be so worried."

"And why would I want to do that?" Chuck responded. Jack smirked and got up from his chair. He picked up his black leather briefcase and nodded towards Chuck. He left the room and Chuck followed him with a look of resentment. He banged his glass onto his desk and ran a hand through his hair. Jack infuriated him like no other. It was as if he was a living reminder of his father determined to destroy his every move.

Chuck got up to get another scotch and heard movement coming from the doorway. Nate entered and sat in the seat that Jack was in a couple of minutes ago.

"What did the jackass want?" Like Chuck, Nate shared the same resentment towards Jack. Nate was the only person Chuck could rely on and he was lucky that like him, Nate could see through the bullshit that Jack threw at them.

"Darling Jack has cordially invited me to 21 on Thursday to 'see for myself what I should be worried about'" Chuck mimicked his uncle's deep tone whilst pouring Nate a drink.

"And are you gonna go?" Nate questioned, taking the glass from Chuck and readjusting his seating position so that he was sat upright. Chuck shrugged his shoulders.

"Yes. No. I don't know." This was the first time in a long time that Nate had seen Chuck indecisive about anything. Ever since they were kids, Chuck had known his plans for life. They may have only included business, girls and booze but that was the path that Chuck had wanted to take. "A part of me wants to, to see what he's so buzzed about. But a part of me thinks why should I?" Chuck downed his scotch. "Why should I go to his pitiful club when I've got Victrola?" Chuck questioned rhetorically.

Nate gave Chuck a look of sympathy. He could see why Chuck was torn. Pride was a big thing to Chuck and going to 21 like Jack had told him would be like a sign of admitting defeat to Chuck, even if technically there was nothing being defeated.

"I think you should go Chuck" Nate urged. "I mean what have you got to lose? You said it yourself, you've got Victrola. Business is pretty damn good at the moment. Now that may be due to my alcoholic expertise," Nate said jokingly and Chuck gave a small smile, raising his eyebrows, "But your corporate talents are putting Victrola at the top." Chuck knew Nate was right. Going to see Jack's damn club wouldn't change what they had at Victrola.

"You're right. Fine, I'll go but you're coming with me Nathaniel. Safety in numbers." Chuck smirked towards his friend. Nate winked at Chuck and downed the rest of his scotch. They made a pretty good team, him and Nate and no Jack-ass could come between that.

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Hope you enjoyed it! Please leave a review so I know what you think!

I had to add in the Chuck and Nate bromance because I just love it too much. I'm also going to try and add in other GG characters to make it as authentic as possible!  
Next chapter will involve Chuck and Nate venturing to Jack's club and Chuck sees something that takes his breath away..


	2. Welcome to Burlesque

**Sorry for the slow update but I've been swamped with schoolwork and I've been really ill for the last week but I was inspired to update nevertheless by your kind reviews! I'm glad you enjoyed the first chapter and in this installment we see the introduction of Blair in Jack's club. What will Chuck's reaction be? Read to find out... (Hope you enjoy!)**

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**Chapter Two**_ - Welcome to Burlesque_

Chuck and Nate were greeted by the melodic sounds of a jazz ensemble and short-skirted waitresses carrying trays of sumptuous alcohol. Chuck was impressed. 21 was now actually a half-decent club. _Good_, he thought to himself. _Things were getting a little dull around here_. They walked through the saloon doors into the bustling atmosphere and walked over to the reserved booth awaiting them. Chuck took off his trench coat and sat down with Nate following suit. Both men were dressed to kill – Chuck wore his signature, eccentric dark grey pinstripe suit, white crisp shirt and scarlet red bow tie whilst Nate wore a more modest black suit and silk cravat combination. They oozed wealth and meant business.

"So far, so good. Nothing on us though, Chuck.' Nate assured Chuck. He could sense his best friend's tension. Nate was a master on reading Chuck – they had been best friends ever since kindergarten, practically brothers. Both boys had their fair shares of troubles growing up. They grew up in a world full of dishonesties, fabrications and deceit – it was a wonder they hadn't grown up to be a pair of warped, manipulated clone of their dearest mothers and fathers. Chuck and Nate could still be manipulative however. Manipulative, indeed.

Chuck merely nodded his head. He was watching. Watching and taking it all in. Chuck was a business man alright. He knew the art of observation and adaptation. He could sense competition and more importantly – he knew how to crush them.

"Mr. Bass and Mr. Archibald, can I get you anything?" A female voice spoke breaking the hostility between the pair. They both looked up to see a tall, tanned waitress standing over them. She had a mass of wild, jet black hair and she wore a crimson corset with lace stockings. Normally, this would be the type of woman Chuck would go for. But not tonight, not with one of Jack's desperate femme fatales.

"A whiskey for me and a scotch for him." Nate stated.

"Sure." The waitress gave her best enticing guise directly to Chuck which he returned with a cold glare. She simpered off to fetch their drinks and Chuck leant back into the leather divan, folding one leg on top of the other.

"Have you seen Jack around?" Chuck inquired.

"No man. I've been looking but I can't see him." Nate replied, "Probably in his office with some female company."

The edges of Chuck's lips curled. Nate was right. If there was any man who was more of a womanizing player than he was, it was his Uncle. At least Chuck had standards.

The waitress returned with their drinks and Chuck downed his in one. He slid the glass along the table in the direction of the woman.

"I'll have another. And make it a double. Especially if Jack's paying." The waitress bent down to show an excess of cleavage and Chuck simply stared at her. Oh, how he loved it when he had a woman right in the palm of his hands. It made the rejection just that bit sweeter.

"And another for my good friend, Nathaniel. In fact, keep them coming."

"No problem, Mr. Bass." The waitress replied with a flirtatious gaze. "Call me Vanessa."

"Thank you, Vanessa." Chuck leant back in his seat and watched her simper away.

For the next hour, awaited the arrival of Jack through consuming copious scotches and whiskeys while the colours of the club blurred into one. The music blared throughout the dingy club and the boys simply took it all in.

Their peace was interrupted when a familiar silhouette made his way onto the vast stage opposite the two friends. Nate nudged Chuck to bring him out of his drunken bliss.

"Took his time." Chuck stated judgmentally.

"Fine customers, it is my pleasure to introduce a first to 21. She is a talented songstress, ready to welcome you to Burlesque." Chuck instantly sat upright, his insides were filled with anger and rage. Burlesque? But that was the whole point of his club! Nate looked towards his friend and shared his mutual wrath. How dare Jack steal Victrola's significance like this…

"Ladies and gentlemen, put your hands together for Miss Blair Waldorf."

The crowd raptured in applause as the house lights went down. The applause slowly transformed into silence as a petite figure took to the stage. The buzzing atmosphere was mutely electrified by this one woman who had the audience's attention in the palm of her hands.

A spotlight illuminated the petite frame of the girl's body and Chuck's anger instantly went away. Her back faced the audience and she was wearing an oyster silk slip that was complimented with cream lace Falke stockings showing a generous amount of her soft thighs. Chuck was captivated.

Blair had lustrous, chocolate brown locks that were styled in loose ringlets. Her face was still hidden but Chuck Bass already knew this would be the most beautiful woman he ever laid his eyes on. He was well and truly under her spell.

The soft rhythm of the harmony began to play as Blair turned her body to face the audience slowly, her front even more beautiful. Chuck couldn't imagine taking his eyes away. He desperately tried to make eye contact with the woman. His harsh brown searching for her soft chocolate pools. The spotlight emphasised her tender, rouge cheekbones as she lifted her head, a smirk forming on her traffic-stopping lips.

_Show a little more,  
show a little less.  
Add a little smoke,  
welcome to Burlesque._

Her crimson red lips enunciated each word perfectly. Her sensual movements had each and every member of the audience entranced. Especially Chuck Bass.

_Everything you dream of,  
but never can possess.  
Nothing's what it seems,  
welcome to Burlesque._

_Oh, everyone is buying,  
put your money in my hand.  
If you got a little extra,  
well, give it to the band._

She gave a kiss on the head of the piano player and gave a cheeky wiggle. She had the audience in raptures of laughter. Even Chuck stifled a little laugh. Nate looked over to his best friend and saw that this singer had him in a trance. Nate had never seen that look on his friend – he was always the love them and leave them type. Business always came before a serious relationship. Maybe this signaled a change in Chuck, maybe he was a changed man.

_You may not be guilty,  
but you're ready to confess.  
Tell me what you need,  
welcome to Burlesque._

Blair was joined on stage by various other exotic dancers who circled her as she continued to sing. Not one of the barely-dressed risqué dancers compared to Blair though. She stole the show.

_You can dream of cocoa,  
do it at your risk.  
The triplets grant you mercy,  
but not your every wish._

_Yes, it keeps you guessing,  
so cool and statuesque.  
"Behave yourself" says Georgia,  
welcome to Burlesque._

_Oh, everyone is buying,  
put your money in my hand.  
If you want a little extra,  
well, you know where I am._

Blair sashayed graciously through the crowd, sitting on few gentlemen's laps as she journeyed through the club.

_Something very dark,  
is playing with your mind.  
It's not the end of days,  
just a bump and grind._

Blair continued her journey through the club until she reached the back wall where Chuck and Nate were sitting. Chuck leant forwards in his seat as his and Blair's eyes met. It was an instant connection, a magnetic pull. Neither one wanting to be the first to look away. It was as if Nate or nobody else was in the club – just them. Chuck and Blair. Blair and Chuck.

Blair gave a sensual smile as she danced in front of Chuck, who was sitting no more than a metre away from her. Eventually, she walked away returning to the stage. Her face still meeting his gaze over her tiny shoulder. Her hips moved erotically to the definite tempo of the band.

_Show a little more,  
show a little less.  
Add a little smoke,  
welcome to Burlesque._

The spotlight faded to black and Blair was nowhere to be seen. Chuck wanted more of her; _needed_ more of her.

"I have to find this girl." Chuck stated to his friend. "I have to bring her to Victrola, Nate."

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**Hope you liked Chapter 2! Next chapter will be Chuck and Blair interaction, I promise! I also promise to try and get a faster update asap!  
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**Please review, xoxo.  
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